Efficient synthesis of 3,4-dihydropyrimidin-2-ones in low melting tartaric acid-urea mixtures

被引：182

作者：

Gore, Sangram ^{[1
,2
]}

Baskaran, Sundarababu ^{[1
]}

Koenig, Burkhard ^{[2
]}

机构：

[1] Indian Inst Technol, Dept Chem, Madras 600036, Tamil Nadu, India

[2] Univ Regensburg, Inst Organ Chem, D-93040 Regensburg, Germany

来源：

GREEN CHEMISTRY | 2011年 / 13卷 / 04期

关键词：

ONE-POT SYNTHESIS; ORGANIC-REACTIONS; SALT MIXTURES; CONDENSATION; ALKALOIDS; SOLVENTS; TRIFLATE;

D O I：

10.1039/c1gc00009h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general, efficient and green method for the synthesis of dihydropyrimidinones is described under mild conditions employing low melting mixtures of L-(+)-tartaric acid and urea derivatives as a novel reaction medium. The melt plays a triple role: as solvent, as catalyst and as reactant, furnishing highly functionalized dihydropyrimidinones in good to excellent yields.

引用

页码：1009 / 1013

页数：5

共 41 条

[1] The tethered Biginelli condensation in natural product synthesis [J].

Aron, ZD ;

Overman, LE .

CHEMICAL COMMUNICATIONS, 2004, (03) :253-265

[2] Greener media in chemical synthesis and processing [J].

Avalos, Martin ;

Babiano, Reyes ;

Cintas, Pedro ;

Jimenez, Jose L. ;

Palacios, Juan C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (24) :3904-3908

[3]

Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360

[4] HYDROPHOBIC EFFECTS ON SIMPLE ORGANIC-REACTIONS IN WATER [J].

BRESLOW, R .

ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (06) :159-164

[5] Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility [J].

Cave, GWV ;

Raston, CL ;

Scott, JL .

CHEMICAL COMMUNICATIONS, 2001, (21) :2159-2169

[6] Osmium tetroxide in poly(ethylene glycol) (PEG): a recyclable reaction medium for rapid asymmetric dihydroxylation under Sharpless conditions [J].

Chandrasekhar, S ;

Narsihmulu, C ;

Sultana, SS ;

Reddy, NR .

CHEMICAL COMMUNICATIONS, 2003, (14) :1716-1717

[7]

Clark J, 1998, CHEM BRIT, V34, P43

[8] Untitled [J].

Clark, J .

GREEN CHEMISTRY, 1999, 1 (02) :G29-G30

[9] Ionothermal synthesis of unusual choline-templated cobalt aluminophosphates [J].

Drylie, Ewan A. ;

Wragg, David S. ;

Parnham, Emily R. ;

Wheatley, Paul S. ;

Slawin, Alexandra M. Z. ;

Warren, John E. ;

Morris, Russell E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (41) :7839-7843

[10] Researches on pyrimidines CXXXIII Some reactions and derivatives of 2-keto-4-phenyl-5-carbethoxy-6-methyl-1,2,3,4-tetrahydropyrimidine [J].

Folkers, K ;

Johnson, TB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1933, 55 :2886-2893

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